Ice colors of the quinoline series



United States Patent ICE COLORS OF THE QUINOLINE SERIE Frederick Brody, New York, N. Y., assignor to American Cyanamid Company, New York, N. Y., a corporation of Maine No Drawing. Original application March 1, 1952, Serial No. 274,489, now Patent No. 2,694,714, dated November 16, 1954. Divided and this application January 14, 1954, Serial No. 404,126

4 Claims. (Cl. 260-155) The present invent-ion relates to compounds of the formula:

N==NR1 o-Nn in which Q is a radical selected from the group consisting of 2-quinoline and its homologues, R is lower alkyl and R1 is a residue of an ice-color coupling component.

The production of azoic coloring matters of a greenish blue shade has presented a considerable problem in the past, as most blue azo coloring matters do not have this desirable shade, or if they do have, have other undesirable characteristics, such as inadequate fastness, high cost, etc. Compounds of the present invention when R1 is the residue of 2-hydroxy-3-naphthoic acid arylides are blue azo dyestufis of good fastness properties and desirable greenish shade.

While in its broader aspects the present invention includes compounds in which Q is quinoline or its homologs, the compound of greatest practical interest is the 4-methyl derivative, which compounds have the formula in which R and R1 have the same meaning as above.

While the present invention is not limited to any particular method of preparing the compounds, I have found that a simple method is the condensation of a 2,5 -dialkoxy 4-amino acylanilide, such as 2,5-dialkoxy-4-aminoacetanilide, with a 2-chloroquinoline, such as 2-chlorolepidine.

The acyl amino compounds are readily hydrolyzed to the free base by known methods. The acyl group can be any lower acyl group, such as acetyl, propionyl, etc., but because of lower price and ready availability, 2,5 dialkoxy-4-aminoacetanilides are preferred. The lower alkyl group represented by R in the formula may be any of the typical lower alkyls, such as ethyl, methyl, propyl, etc.

The free bases used in the present invention are diazotized smoothly and coupled with ordinary coupling components, either to prepare pigments or to dye goods by padding the coupling component thereon and developing, or by forming stable derivatives of the diazo compounds, such as diazoamino compounds, which can he incorporated in printing pastes and developed onthe fiber by acid development. Among the coupling components which may be used are such compounds as beta-naphthol, 8-amino-2-naphthol, 8-acetylarnino-Z-naphthol, benzyl naphthols, pyrazolones and pyrazyl pyrazolones, hydroxybenzofluorenones and the various N-substituted amides such as arylides of 2-hyd'roxy-3-naphthoic acid, of 2-hydroxy-3-anthroic acid, of methyl and dirnethylsali- I 2,725,376 I Patented Nov- 29,

'2 cylic acids, of hydroxycarbazole' carboitylic acids, of lay droxybenzocarbazole carboxylic acids, of hydroxybenzothiophene carboxylic acids, of acetoace'tic acid. of benzoylacetic acid and the like.

The free bases used in producing the dyestuffs of the present invention are themselves new chemical compounds. They are not claimed in the present application, forming the subject matter of my copending application Serial No. 274,489, filed March 1, 1952, now Patent No. 2,694,714 of which the present application is a division.

This invention is further illustrated by the following examples. Where not otherwise noted, parts are by weight.

Example 1 on, oirno NHC O C H3 CzHs I A mixture of 7.14 parts of 2,5-diethoxy-4-aminoacetanilide, 5.33 parts of 2-chlorolepidine and 3 parts of N hydrochloric acid in parts of 50% dioxane-water is refluxed until condensation is complete and then drowned in Water. The product is filtered and may be recrysta1 lized from alcohol or from a mixture of dioxane and ethyl acetate. It is the hydrochloride of the compound of the above formula. It is readily converted by ordinary methods to the free base, which may be recrystallized from alcohol.

Example 2 CH: CiHsO NH N [13ml I Cotton cloth is padded with an alkaline solution of 2- hydroxy-3-naphthoic anilide and developed with the diazo solution prepared in the ordinary way from the aboveprepared base. Blue dyeings are obtained of very green OH JONHCQH;

shade.

Example 4 O C iHl NI Ia I NH N The procedure of Examples 1 and 2 is followed, re-

I claim: a

1. An azoic coloring matter having theformula N==NR1 Q-NH inwhich Q is a radical selected from the group consisting of Z-quinoline and its homologues, R is lower alkyl and R1 is a residue of an ice-color coupling component of the naphthalene series.

2. An azoic coloring matter having the formula in which R is lower alkyl and Ri is the residue of an icecolor coupling component of the naphthalene series.

3. An azoic coloring matter having the formula OH O ONHCGHG C H3 0 R I N=Ng I LNH N in which R is lower alkyl.

4. An azoic coloring matter having the following for mula OH O ONHCuHs No references cited. 

1. AN AZOIC COLORING MATTER HAVING THE FORMULA 